Synthesis of some 16,17-secoandrost-5-ene derivatives
Starting from 3β-acetoxy-17-oxo-16,17-secoandrost-5-ene-16-nitrile (1), 3β-acetoxy-16,17-secoandrost-5-ene-16-nitrile (4) was synthesized by a three-stage procedure. First, the formyl group of compound 1 was reduced, to yield the alcohol 2. Compound 2 was further transformed to the mesyloxy derivati...
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| Format: | Article |
| Language: | English |
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Association of Chemical Engineers of Serbia
2010-01-01
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| Series: | Hemijska Industrija |
| Subjects: | |
| Online Access: | http://www.doiserbia.nb.rs/img/doi/0367-598X/2010/0367-598X1000009G.pdf |
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| author | Gaković Andrea R. Đurendić-Brenesel Maja Đ. Đurendić Evgenija A. Penov-Gaši Katarina M. Sakač Marija N. |
| author_facet | Gaković Andrea R. Đurendić-Brenesel Maja Đ. Đurendić Evgenija A. Penov-Gaši Katarina M. Sakač Marija N. |
| author_sort | Gaković Andrea R. |
| collection | DOAJ |
| description | Starting from 3β-acetoxy-17-oxo-16,17-secoandrost-5-ene-16-nitrile (1), 3β-acetoxy-16,17-secoandrost-5-ene-16-nitrile (4) was synthesized by a three-stage procedure. First, the formyl group of compound 1 was reduced, to yield the alcohol 2. Compound 2 was further transformed to the mesyloxy derivative 3, whose reduction with NaBH3CN gave compound 4. Apart from compound 4 as the main reaction product, two additional products were obtained, for which the GC/MS analysis suggested that they are 8(14) and 14 derivatives of compound 4. Compound 4 was transformed into 3β-hydroxy-16,17-sesoandrost-5-ene-16-nitrile (7), the Oppenauer oxidation of which afforded 3-oxo-16,17-secoandrost-4-ene-16-nitrile (8). |
| first_indexed | 2024-12-12T04:23:27Z |
| format | Article |
| id | doaj.art-4c22ff2b4c13481faf974d4c902f3376 |
| institution | Directory Open Access Journal |
| issn | 0367-598X |
| language | English |
| last_indexed | 2024-12-12T04:23:27Z |
| publishDate | 2010-01-01 |
| publisher | Association of Chemical Engineers of Serbia |
| record_format | Article |
| series | Hemijska Industrija |
| spelling | doaj.art-4c22ff2b4c13481faf974d4c902f33762022-12-22T00:38:15ZengAssociation of Chemical Engineers of SerbiaHemijska Industrija0367-598X2010-01-01642818410.2298/HEMIND100212009GSynthesis of some 16,17-secoandrost-5-ene derivativesGaković Andrea R.Đurendić-Brenesel Maja Đ.Đurendić Evgenija A.Penov-Gaši Katarina M.Sakač Marija N.Starting from 3β-acetoxy-17-oxo-16,17-secoandrost-5-ene-16-nitrile (1), 3β-acetoxy-16,17-secoandrost-5-ene-16-nitrile (4) was synthesized by a three-stage procedure. First, the formyl group of compound 1 was reduced, to yield the alcohol 2. Compound 2 was further transformed to the mesyloxy derivative 3, whose reduction with NaBH3CN gave compound 4. Apart from compound 4 as the main reaction product, two additional products were obtained, for which the GC/MS analysis suggested that they are 8(14) and 14 derivatives of compound 4. Compound 4 was transformed into 3β-hydroxy-16,17-sesoandrost-5-ene-16-nitrile (7), the Oppenauer oxidation of which afforded 3-oxo-16,17-secoandrost-4-ene-16-nitrile (8).http://www.doiserbia.nb.rs/img/doi/0367-598X/2010/0367-598X1000009G.pdfandrost-5-ene derivatives16, 17-seco steroidsreduction of aldehydes |
| spellingShingle | Gaković Andrea R. Đurendić-Brenesel Maja Đ. Đurendić Evgenija A. Penov-Gaši Katarina M. Sakač Marija N. Synthesis of some 16,17-secoandrost-5-ene derivatives Hemijska Industrija androst-5-ene derivatives 16, 17-seco steroids reduction of aldehydes |
| title | Synthesis of some 16,17-secoandrost-5-ene derivatives |
| title_full | Synthesis of some 16,17-secoandrost-5-ene derivatives |
| title_fullStr | Synthesis of some 16,17-secoandrost-5-ene derivatives |
| title_full_unstemmed | Synthesis of some 16,17-secoandrost-5-ene derivatives |
| title_short | Synthesis of some 16,17-secoandrost-5-ene derivatives |
| title_sort | synthesis of some 16 17 secoandrost 5 ene derivatives |
| topic | androst-5-ene derivatives 16, 17-seco steroids reduction of aldehydes |
| url | http://www.doiserbia.nb.rs/img/doi/0367-598X/2010/0367-598X1000009G.pdf |
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